Hydrocarbon polymers and oligomers with polar end groups, especially telechelic polymers and oligomers, are very important and useful building blocks for many chemical syntheses and processes. However the many applications of these polymers and oligomers are hindered by the limited availability of such functional polymers and oligomers. Currently most of the commercially available telechelic hydrocarbon polymers are based on polybutadienes, which are produced by a radical process to generate hydroxyl groups at both the chain ends. Further chemical reactions can convert the hydroxyl groups to some other functional groups such as carboxylic acids, amines and isocyanates. However these processes have poor controllability and tunability. As a result, very limited properties, such as molecular weight, comonomer content, thermal and rheological properties, can be provided. Thus, there is a demand for more versatile processes to generate a wide variety of telechelic polymers and oligomers for many applications.
Currently, no method is available for selective oxidative cleavage of hydrocarbon polymers or cyclic molecules with internal alkenes to generate telechelic hydrocarbon polymers or oligomers with controlled properties such as molecular weight and/or crystallinity.
An example of oxidative cleavage of alkenes is “Oxidative Cleavage of Alkenes Using an In Situ Generated lodonium Ion with Oxone as a Terminal Oxidant”, Prem P. Thottumkara and Thottumkara K. Vinod; Organic Letters 2010, 12, pp. 5640-5643.
An example of epoxidation of alkenes (such as dodecene) with sodium periodate is found at Applied Catalysis A: General 370 (2009) pp. 66-71.
Other references of interest include: WO 00/32645 and Macromolecules 2003, 36, 7027-7034; Synthesis (1989) (1) pp. 47-48.